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4887-88-1 Usage

Chemical Properties

off-white powder

Check Digit Verification of cas no

The CAS Registry Mumber 4887-88-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,8,8 and 7 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 4887-88:
(6*4)+(5*8)+(4*8)+(3*7)+(2*8)+(1*8)=141
141 % 10 = 1
So 4887-88-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H5BrN2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10)

4887-88-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Aldrich

  • (702188)  6-Bromo-1H-benzimidazole  97%

  • 4887-88-1

  • 702188-1G

  • 575.64CNY

  • Detail
  • Aldrich

  • (702188)  6-Bromo-1H-benzimidazole  97%

  • 4887-88-1

  • 702188-5G

  • 1,918.80CNY

  • Detail
  • Aldrich

  • (L510343)  5-Bromo-1H-benzo[d]imidazole  AldrichCPR

  • 4887-88-1

  • L510343-1G

  • 644.67CNY

  • Detail

4887-88-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-1H-benzimidazole

1.2 Other means of identification

Product number -
Other names 5-Bromo-1H-benzo[d]imidazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4887-88-1 SDS

4887-88-1Synthetic route

formic acid
64-18-6

formic acid

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
at 100℃;100%
With hydrogenchloride In water for 3h; Reflux;97.5%
for 2h; Reflux;85%
With hydrogenchloride
Stage #1: formic acid; 4-Bromo-benzene-1,2-diamine for 2h; Reflux;
Stage #2: With sodium hydroxide In water at 20℃;
4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
Stage #1: 4-Bromo-benzene-1,2-diamine; trimethyl orthoformate With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide pH=7;
100%
With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;100%
With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;100%
With formic acid at 80℃; for 16h;
formic acid
64-18-6

formic acid

4-bromo-1,2-dinitrobenzene
610-38-8

4-bromo-1,2-dinitrobenzene

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction;96%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With zirconium(IV) chloride In methanol at 20℃; for 3h;95%
at 125℃;79%
formic acid at 80℃; for 18h;
carbon dioxide
124-38-9

carbon dioxide

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With 4-dimethylamino-benzaldehyde In 1-methyl-pyrrolidin-2-one at 120℃; under 7500.75 Torr; for 24h; Flow reactor;91%
With bis[1,2-bis(diphenylphosphine)ethane]ruthenium dichloride; hydrogen at 120℃; under 112511 Torr; for 40h; Green chemistry;90%
5-bromo-2-mercaptobenzimidazole
68468-39-3

5-bromo-2-mercaptobenzimidazole

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With rose bengal; water; oxygen; sodium chloride In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;90%
Aminoiminomethanesulfinic acid
1758-73-2

Aminoiminomethanesulfinic acid

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
In water at 60℃; for 1h;89%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With Imidazole hydrochloride at 120℃; for 6h;88%
With Triethoxysilane; carbon dioxide; tris(pentafluorophenyl)borate at 120℃; for 24h;94 %Spectr.
carbon dioxide
124-38-9

carbon dioxide

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

A

5-bromo-1-methyl-1H-benzo[d]imidazole
53484-15-4

5-bromo-1-methyl-1H-benzo[d]imidazole

B

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With phenylsilane at 50℃; under 22502.3 Torr; for 3h; Pressure; Autoclave;A 7%
B 88%
oxalic acid
144-62-7

oxalic acid

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
In 1,4-dioxane at 120℃; for 6h; Green chemistry;85%
methanol
67-56-1

methanol

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 130℃; for 48h; Autoclave;85%
formic acid
64-18-6

formic acid

4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With iron; ammonium chloride In isopropyl alcohol at 80℃; Inert atmosphere; Schlenk technique;85%
With iron; ammonium chloride In isopropyl alcohol at 80℃; for 3h; Inert atmosphere;82%
D-Glucose
2280-44-6

D-Glucose

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; trifluorormethanesulfonic acid; water at 100℃; for 1h; Sealed tube;81%
benzoimidazole
51-17-2

benzoimidazole

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 3h;77%
4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

Aminoiminomethanesulfinic acid
1758-73-2

Aminoiminomethanesulfinic acid

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 70℃; for 1.5h; Green chemistry;68%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
With ammonium acetate; water at 140℃; for 10h; Inert atmosphere; Schlenk technique;67%
formaldehyd
50-00-0

formaldehyd

4-bromo-phenylene-diamine-(1.2)

4-bromo-phenylene-diamine-(1.2)

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

formic acid
64-18-6

formic acid

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
at 80℃; for 16h;
4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / H2NNH2; FeCl3*6H2O / methanol
2: 79 percent / 125 °C
View Scheme
2-phenoxy-1-phenylethanone
721-04-0

2-phenoxy-1-phenylethanone

4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

A

5-bromo-2-phenyl-1H-benzo[d]imidazole
1741-50-0

5-bromo-2-phenyl-1H-benzo[d]imidazole

B

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 2-methoxy-ethanol at 120℃; for 24h; Sealed tube;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole
1214899-89-4

5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 18h; Inert atmosphere;100%
With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 18h; Inert atmosphere;100%
With C21H17F3N6O2*C7H8O3S In tetrahydrofuran at 60℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

1,1-dimethylethyl 5-bromo-1H-benzimidazole-1-carboxylate
942590-05-8

1,1-dimethylethyl 5-bromo-1H-benzimidazole-1-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;98%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;98%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;98%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

cyclopropylboronic acid
411235-57-9

cyclopropylboronic acid

A

1-cyclopropyl-5-vinylbenzimidazole

1-cyclopropyl-5-vinylbenzimidazole

B

1-cyclopropyl-6-vinylbenzimidazole

1-cyclopropyl-6-vinylbenzimidazole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole; cyclopropylboronic acid With [2,2]bipyridinyl; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 80℃; under 775.743 Torr; for 48h;
Stage #2: pinacol vinylboronate With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 16h;
A 85.79%
B 85.79%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

5-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: p-methoxybenzyl chloride In tetrahydrofuran at 60℃; for 3h; Temperature;
78%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole
444103-78-0

5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide
77%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 4h;
75%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;
44%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil for 1h; Inert atmosphere;
44%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

C11H13NO4S

C11H13NO4S

C18H18BrN3O4S

C18H18BrN3O4S

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole With potassium carbonate In acetonitrile at 50℃; for 0.666667h;
Stage #2: C11H13NO4S In acetonitrile at 75℃;
73%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

C11H13NO4S

C11H13NO4S

C18H18BrN3O4S

C18H18BrN3O4S

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole With potassium carbonate In acetonitrile at 70℃; for 0.5h;
Stage #2: C11H13NO4S In acetonitrile at 20 - 70℃;
72.8%
carbon dioxide
124-38-9

carbon dioxide

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

5-benzimidazolecarboxylic acid
15788-16-6

5-benzimidazolecarboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-benzo[d]imidazole With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h;
Stage #3: carbon dioxide In tetrahydrofuran; hexane at -20℃; for 0.5h;
71%
2-nitrophenylboronic acid
5570-19-4

2-nitrophenylboronic acid

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

5-(2-nitrophenyl)-1H-benzo[d]imidazole

5-(2-nitrophenyl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
In water66%
benzyl (2,2-dimethylbut-3-ynoyl)-L-leucyl-L-valyl-L-phenylalaninate

benzyl (2,2-dimethylbut-3-ynoyl)-L-leucyl-L-valyl-L-phenylalaninate

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

benzyl (2-(1-(1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-4-yl)-2-methylpropanoyl)-L-leucyl-L-valyl-L-phenylalaninate

benzyl (2-(1-(1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-4-yl)-2-methylpropanoyl)-L-leucyl-L-valyl-L-phenylalaninate

Conditions
ConditionsYield
With copper(l) iodide; sodium azide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium L-ascorbate In water; dimethyl sulfoxide at 70℃; for 4h; Inert atmosphere;66%
2-nitrophenylboronic acid
5570-19-4

2-nitrophenylboronic acid

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

[2-(1H-1,3-benzodiazol-5-yl)phenyl]azinic acid

[2-(1H-1,3-benzodiazol-5-yl)phenyl]azinic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere;66%
5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

5-bromo-4,6,7-triiodo-1H-benzimidazole
1196457-08-5

5-bromo-4,6,7-triiodo-1H-benzimidazole

Conditions
ConditionsYield
With sulfuric acid; iodine; periodic acid at 60℃; Cooling with ice;65%
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

5-bromo-1H-benzo[d]imidazole
4887-88-1

5-bromo-1H-benzo[d]imidazole

A

6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole
1299292-27-5

6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole

B

5-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole
1299292-26-4

5-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 3h; Reflux;A 36%
B 61%
Stage #1: 5-bromo-1H-benzo[d]imidazole With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane for 24h; Reflux;
Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 2h; Reflux;
A 29%
B 24%

4887-88-1Relevant academic research and scientific papers

Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles

An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong

supporting information, p. 748 - 753 (2022/02/02)

We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao

supporting information, (2022/02/07)

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal

supporting information, p. 3754 - 3759 (2021/10/14)

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.

Highly Efficient and Catalyst-Free Synthesis of Benzimidazoles in Aqueous Media

Huang, W.-H.,Jin, Y.-J.,Ma, L.-F.,Wu, Y.,Zhou, L.-H.

, p. 825 - 830 (2021/06/12)

Abstract: A convenient and highly efficient, catalysts-free synthesis of benzimidazoles in an aqueous medium has been developed. The conditions of the synthesis were optimized, and its scope was successfully extended to various substrates with good to excellent yields. The experimental procedure is simple, and the products can be isolated by filtration followed by recrystallization from water.

Hetero- A nd Homobimetallic Complexes Bridged by a Bis(NHC) Ligand: Synthesis via Selective Sequential Metalation and Catalytic Applications in Tandem Organic Transformations

Nishad, Rajeev C.,Kumar, Shashi,Rit, Arnab

, p. 915 - 926 (2021/05/04)

A (bis)azolium salt [L1-H2]Br2 (5), synthesized following multistep procedures, was realized to be a suitable platform for accessing the bis(NHC) ligand supported heterobimetallic IrIII-M (M = PdII/AuI) complexes via a sequential metalation strategy for their potential catalytic applications in one-pot tandem organic transformations. First, the reaction of 5 with 0.5 equiv of [Ir(Cp-)Cl2]2 selectively yielded a monometallic IrIII complex 6, which was further metalated using Pd(OAc)2/NaOAc to afford the heterobimetallic IrIII-PdII complex 7. On the other hand, complex 6 was reacted with Ag2O, followed by transmetalation with [Au(SMe2)Cl] in a one-pot manner, to yield the IrIII-AuI complex 8. Further, the related homobimetallic IrIII and PdII complexes 9 and 10, respectively, have also been synthesized directly from [L1-H2]Br2. All the homo/heterobimetallic complexes have been well-characterized by multinuclear NMR spectroscopy, ESI-mass spectrometry, and via single-crystal X-ray diffraction studies of the complexes 7, 8, and 10. The heterobimetallic IrIII-PdII complex 7 has been tested as a catalyst for three one-pot tandem catalytic reactions: (a) Suzuki-Miyaura coupling and transfer hydrogenation of ketones, (b) hydrodefluorination and transfer hydrogenation of ketones, and (c) hydrodehalogenation and transfer hydrogenation of imines. Importantly, the catalytic activity of heterobimetallic complex 7 in the above-mentioned reactions was found to be better than the mixture of their corresponding homobimetallic counterparts 9 and 10, keeping the concentration of the metal centers constant. These observations affirm some sort of cooperativity between the two metal centers (Ir and Pd) connected via a single ligand frame in 7 when catalytic activity is concerned, which thus constitutes a superior catalytic system than that of the cases where two separate metal complexes (hence, the two metal centers are not connected by a single ligand framework) are used.

Poly(3-hexylthiophene)s Functionalized with N-Heterocyclic Carbenes as Robust and Conductive Ligands for the Stabilization of Gold Nanoparticles

Sun, Ningwei,Zhang, Shi-Tong,Simon, Frank,Steiner, Anja Maria,Schubert, Jonas,Du, Yixuan,Qiao, Zhi,Fery, Andreas,Lissel, Franziska

supporting information, p. 3912 - 3917 (2020/12/30)

Recently, N-heterocyclic carbenes (NHCs) are explored as anchor groups to bind organic ligands to colloidal gold (i.e. gold nanoparticles, Au NPs), yet these efforts are confined to non-conjugated ligands so far—that is, focused solely on exploiting the s

Method for synthesizing benzimidazole from carbon dioxide and o-phenylenediamine compound

-

Paragraph 0033-0036, (2021/06/06)

The invention discloses a method for synthesizing benzimidazole from carbon dioxide and an o-phenylenediamine compound, the method is characterized in that an amino-containing functionalized ordered mesoporous polymer is used as a catalyst, o-phenylenediamine and carbon dioxide are used as raw materials, dimethylaminoborane is used as a hydrogen reduction reagent, carbon dioxide and the o-phenylenediamine compound are catalyzed to react in an NMP solvent to generate a benzimidazole compound, wherein the dosage of a catalyst is 0.01-1mol% based on the nitrogen content of the o-phenylenediamine compound; the filling pressure of the carbon dioxide is 0.1-2MPa; the reaction temperature is 60-180DEG C; the molar ratio of the catalyst to the NMP is 1:50-100. Compared with the prior art, the catalyst has the advantages of simple preparation, high catalytic activity, capability of catalyzing the reaction of carbon dioxide and the o-phenylenediamine compound under mild conditions to generate benzimidazole and derivatives thereof, and the like.

Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives

Han, Limin,Hong, Hailong,Li, Xiao,Yang, Yue,Zhang, Junhua,Zhu, Ning

supporting information, (2021/09/28)

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.

Highly efficient one pot synthesis of benzimidazoles from 2-nitroaniline and PhSiH3 as reducing agent catalyzed by Pd/C as a heterogeneous catalyst

Phatake, Vishal V.,Bhanage, Bhalchandra M.

, (2021/03/15)

This work reports an efficient route for the synthesis of benzimidazole from o-nitroaniline in the presence of carbon dioxide atmosphere, PhSiH3 as a reducing agent catalyzed by Pd/C as a catalyst. Benzimidazoles have become the focus of organic chemists, as benzimidazole is an important intermediate in medicinal chemistry. We have developed more efficient route for the synthesis benzimidazole and various substituted benzimidazoles have been synthesized in good to excellent yield. The TBD (1,5,7-Triazabicyclo [4.4.0] dec-5-ene) is selected as a base as it promotes the CO2 insertion. Benzimidazoles were synthesized through reduction of nitro group followed by cyclization of amine using CO2 as a carbon source. Moreover, the Pd/C catalyst can be recycled up to five recycle run without significant changes in the yield of the product.

Endogenous X-C=O species enable catalyst-free formylation prerequisite for CO2reductive upgrading

Dai, Wenshuai,Li, Hu,Saravanamurugan, Shunmugavel,Wu, Hongguo,Yang, Song

, p. 5822 - 5832 (2020/10/21)

CO2, the main component of greenhouse gas, is currently developed as a promising surrogate of carbon feedstock. Among various conversion routes, CO2undergoing catalytic reduction can furnish hydrogen/energy carriers and value-added chemicals, while specific metal-containing catalysts or organocatalysts are often prerequisite for smooth proceeding of the involved reaction processes. In this work, both formic acid and N-containing benzoheterocyclic compounds (including various benzimidazoles, benzothiazole, and benzoxazole) along with silanols could be synthesized with high yields (>90%) from catalyst-free reductive upgrading of CO2under mild conditions (50 °C). The endogenous X-CO species, derived from the N-methyl-substituted amide-based solvent [Me2N-C(O)-R], especially PolarClean, and O-formyl group [O-C(O)-H] of in situ formed silyl formate, were found to play a prominent promotional role in the activation of the used hydrosilane for reductive CO2insertion, as demonstrated by density functional theory (DFT) calculations and isotopic labeling experiments. Moreover, reaction mechanisms and condition-based sensitivity assessment were also delineated.

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